3-hydroxy-1-(2-hydroxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one | 1563186-00-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-hydroxy-1-(2-hydroxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1563186-00-4
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: GGEMGNSPBZYXNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-(2-hydroxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以70%的产率得到2',3',4'-trimethoxyflavone
  参考文献：
  名称：

  Synthesis of 2′,3′,4′-trihydroxyflavone (2-D08), an inhibitor of protein sumoylation

  摘要：

  Protein sumoylation is a dynamic posttranslational modification involved in diverse biological processes during cellular homeostasis and development. Recently sumoylation has been shown to play a critical role in cancer, although to date there are few small molecule probes available to inhibit enzymes involved in the SUMO conjugation process. As part of a program to identify and study inhibitors of sumoylation we recently reported the discovery that 2',3',4'-trihydroxyflavone (2-D08) is a cell permeable, mechanistically unique inhibitor of protein sumoylation. The work reported herein describes an efficient synthesis of 2-D08 as well as a structurally related but inactive isomer. We also report an unanticipated Wessely-Moser rearrangement that occurs under vigorous methyl ether deprotection conditions. This rearrangement likely gave rise to 2-D08 during a deprotection step, resulting in 2-D08 appearing as a contaminant in a screening well from a commercial supplier. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.010
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-hydroxy-1-(2-hydroxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of 2′,3′,4′-trihydroxyflavone (2-D08), an inhibitor of protein sumoylation

  摘要：

  Protein sumoylation is a dynamic posttranslational modification involved in diverse biological processes during cellular homeostasis and development. Recently sumoylation has been shown to play a critical role in cancer, although to date there are few small molecule probes available to inhibit enzymes involved in the SUMO conjugation process. As part of a program to identify and study inhibitors of sumoylation we recently reported the discovery that 2',3',4'-trihydroxyflavone (2-D08) is a cell permeable, mechanistically unique inhibitor of protein sumoylation. The work reported herein describes an efficient synthesis of 2-D08 as well as a structurally related but inactive isomer. We also report an unanticipated Wessely-Moser rearrangement that occurs under vigorous methyl ether deprotection conditions. This rearrangement likely gave rise to 2-D08 during a deprotection step, resulting in 2-D08 appearing as a contaminant in a screening well from a commercial supplier. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.010